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Iodoethane → 4-(Diethylamino)phenethyl alcohol

HRID 1174436
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1174436
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1C=CC=C[CH:19]=1.[CH2:24](I)[CH3:25]>ClCCl>[CH2:18]([N:1]([CH2:24][CH3:25])[C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1)[CH3:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6340IodoethaneHCID 7964ChlorobenzeneHCID 11430Potassium CarbonateHCID 669044-Aminophenethyl alcohol

Produkt 1

HCID 27582364-(Diethylamino)phenethyl alcohol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a four-aperture flask, 9.6 g (70 mmol) of p-aminophenethyl alcohol, 38.7 g (280 mmol) of potassium carbonate, and 100 mL of monochlorobenzene were poured, and the mixture was heated at 120° C. under an argon atmosphere with stirring. Then, 32.8 g (210 mmol) of ethyl iodide was delivered by drops into the mixture for 5 hours. Upon completion of the dripping, the mixture was further heated with stirring for 5 hours. The reaction solution was cooled to the room temperature and then diluted with dichloromethane, followed by washing with water three times. The dichloromethane solution was dried with anhydrous magnesium sulfate, the solvent was distilled away to purify the dichloromethane solution by silica gel chromatography using a mixture solvent of toluene/ethyl acetate (2/1) as an eluent to thereby synthesize 12.1 g (yield: 89% by mass) of p-diethylaminophenethyl alcohol.

Aufarbeitung

  1. temperatureUpon completion of the dripping, the mixture was further heated
  2. stirringwith stirring for 5 hours
  3. temperatureThe reaction solution was cooled to the room temperature
  4. washby washing with water three times
  5. dry with materialThe dichloromethane solution was dried with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away
  7. customto purify the dichloromethane solution by silica gel chromatography
  8. customto thereby synthesize 12.1 g (yield: 89% by mass) of p-diethylaminophenethyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-07c07302c7794ba881d311d0210075a6
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07838188B2

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